Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/07—Aldehydes; Ketones

Definitions

• the present invention is directed to ultra­violet absorbing compositions comprising certain conjugated bis-1,3-diketone derivatives of benzene and blends thereof which are useful as protective coatings and to a method for protecting substrates against the harmful effects of actinic radiation. It is further directed to a process for making ultraviolet absorbing coating compositions.
• Ultraviolet radiation absorbing coatings are useful in protecting substrates such as plastics against accelerated deterioration and the skin of warm blooded animals against severe erythema, edema and blistering when exposed to sunlight.
• the bis-diketone compositions of this invention are generally referred to as sunscreen compositions and blends thereof can be incorporated with waxes, oils, lacquers and soft resins in the preparation of furniture and auto polishes, as well as cosmetics, suntan oils, lotions, lipstick, hair treatments, skin formulations and in addition can be incorporated with contact lenses.
• This invention relates to sunscreen composi­tions comprising a carrier having incorporated therein an effective amount of a ultraviolet absorber selected from a compound of general Formula I: RCOCH2CO-A-COCH2COR1 (I) wherein -R and R1 are independently selected from both linear and branched alkyl groups having from 1 to 10 carbon atoms or from CR2R3Ar where R2 and R3 are selected from H and alkyl groups having 1-4 carbon atoms and Ar is a phenyl or an alkyl substituted phenyl group.
• the group -A- is selected form a bivalent 1,3 or 1,4 benzene radical having Formula II or III.
• R4, R5, R6, R7 are independently selected from H or alkyl groups having from 1 to 10 carbon atoms or alkoxy groups having from 1 to 10 carbon atoms, providing that only one of the groups bonded to the aromatic ring is an alkoxy group.
• Preferred compounds are those where R1 and R are either tert-butyl or isopropyl and R4, R5, R6, R7 are hydrogen.
• the method for protecting substrates com­prise topically applying the compound of formula I in an acceptable carrier.
• an acceptable carrier Of particular interest are compounds which provide selective absorption of UV radiation in the 290-320 nm as well as the 320-400 nm range of wave lengths.
• the compounds may be dissolved in the coating compositions or present as a finely divided solid or as a solid dispersed in an acceptable carrier.
• the selection of carrier used in the coating composition must not interfere with the absorption in the 290-400 nm range. In some instances interaction of the bis-diketone with a carrier shifts absorption outside the desired range and is not acceptable.
• compositions of the invention comprise UV filter compounds of Formula I in amounts needed to provide desired protection against the harmful effects of ultraviolet radiation.
• concentration of the compounds in the composition is regulated such that when the composition is topically applied, the desired protection is provided.
• the amount needed to provide the desired protection can vary with the characteris­tics of the compound, that is, its extinction coeffi­cient or substantively, the nature of the carrier, the source and intensity of the radiation and other well recognized variables. Suitable amounts can be readily determined by standard methods of testing.
• UV filter compounds are incorporated in an amount ranging from about 0.1 percent to about 50 percent by weight and usually in amounts of 1.0-30 percent by weight and preferred amounts ranging from 1.5-15 percent by weight based on the total weight of the coating composition.
• Acceptable carriers include any vehicle or medium capable of incorporating the UV filter compound in a manner permitting uniform topical application.
• pharmaceutically acceptable is intended as a qualifier when the carrier is dermatologically innocuous to warm blooded animals and cosmetically acceptable. However all carriers are not useful on skin.
• the carrier may comprise a wax, oil or cream base material in which the agent can be held in a clear solution or a uniform dispersion for example as submicron sized particles.
• the carrier comprises a suitable solvent or a mixture of solvents capable of dissolving the UV filter compounds to provide a concentration that is effective as a filter­ing agent when incorporated in the sunscreen formulation.
• Solvents which may be useful include alcohols, ketones, esters, polyol esters, oils, hydrocarbons, chlorinated hydrocarbons, ethers, polyethers, polyetherpolyols and other special sol­vents such as dimethylsulfoxide, dimethylformamide, dimethylisosorbide, isopropylmyristate and the like. Such solvents are considered useful only if they do not permanently interact with the active UV filtering compound of the invention to shift the total effective absorption outside the 290-400 nm range. Some of the above named ingredients are not pharmaceutically acceptable but are useful in other applications.
• the invention is directed to method for protecting a substrate against the effects of ultravi­olet radiation which comprises topically applying the above described compounds in a carrier.
• the sunscreening compositions may be applied as a clear liquid or a lotion comprising a water-in-­oil, oil-in-water or a multiple emulsion. Either the oil or water base or both may be used as a carrier for the sunscreening composition.
• the oil base material and the water and oil base compositions will form a continuous film of the UV filtering compound. Such films also provide long lasting protection against sun induced erythema.
• Sunscreening formulations are generally used in hot weather and at beaches where people enjoy bathing activity. It is also essential that the protective coating applied to the skin is not appreciably affected by water or perspiration.
• the pharmaceutically acceptable compositions herein disclosed are included in a thin layer protective coating on the skin of warm blooded animals and provide long lasting protection against erythema and do not appreciable decompose over practical periods of exposure to sunlight.
• the compounds are synthesized by condensing the enolate of the corresponding ketone with a diester such as dimethyl terephthalate in an inert solvent such as tetrahydrofuran or n-butylether.
• R and R1 are alkyl groups
• the substituted aromatic diesters can be prepared according to known methods, such as that described by Wals et al. (Rec Trav. Chim. Pays-Bas 87 p. 65 1968).
• Those compounds wherein R and R1 are CR2R3Ar can be prepared by reacting the corresponding diacetyl benzene with the appropriate ester of phenyl acetic acid or a substituted phenyl acetic acid.
• This material is prepared by repeating the procedure of preparation 1 substituting methyl isopropyl ketone for pinacolone in equivalent molar amounts.
• the product has a peak absorption of 343 nm and a molar extinction coefficient of 32,313.
• This material is prepared by repeating preparation 1 employing stoichiometric amounts of methyl isobutyl ketone in place of pinacolone.
• This solid has a maximum absorption peak at 343 nm and a molar extinction coefficient of 33.000.
• UV filters of the invention can be demonstrated in lotion formulations which are topically applied to the surface of the skin.
• the effectiveness of the UV light absorbers are tested on human subjects by treating a 1 cm square section of a subjects' back with predetermined amounts of lotion, exposing the treated areas to UV light for a period of time and thereafter making a visual comparison with untreated and fully masked skin areas.
• SPF skin protection factor
• Example 3 The solution of Example 3 was applied to 8 specimens of excised hairless mouse epidermis at a level of 1 mg/cm2. The epidermis was exposed to ultraviolet radiation in the UV-B and UV-A range and compared with unprotected skin similarly exposed. Average test results for SPF are listed in Table 2. Table 2 Peak Absorption Mol Extinct Coefficient SPF Standard Deviation (nm) Mol Wt UV-B UV-A UV-B UV-A 344 117.8 1.4 1.43 .35 .26 Control 100% DMI ⁇ 1.0 ⁇ 1.0 0 0 0
• compositions of the invention can also be employed in various formulations such as waxes, oils, lacquers and soft resins in the preparation of furniture and auto polishes, cosmetics, lipstick, hair treatments, skin formulations and contact lenses.
• the compounds of the invention act as filtering agents and may be used singly or in combina­tion to provide a wider range of protection.
• the following formulations are given to demonstrate a few of the many applications. Example No.
• Filtering Agent Carrier Ingredients Composition (% by Wt) 5 Aerosol Hairdressing Prep 4 5.0 Decaglycerol monolaurate 2.0 Polypropylene (200) monooleate 3.0 Ethoxylated (10) lanolin alcohols 1.0 Propylene glycol 2.0 Ethyl alcohol, anhydrous 39.5 Protein polypeptide (20% alcoholic) 1.2 Isopropyl myristate 1.3 Propellant 11 15.0 Propellant 12 30.0 Water q.s. Procedure for Formula: Dissolve all ingredients in slightly warmed ethylalcohol, avoiding loss of the alcohol, add the water, and agitate well to disperse any haze. Filter the concentrate and fill into aerosol containers. Add propellants.

Landscapes

• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Polymers & Plastics (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Emergency Medicine (AREA)
• Organic Chemistry (AREA)
• Medicinal Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Dermatology (AREA)
• Cosmetics (AREA)

Applications Claiming Priority (2)

Publications (2)

Family

ID=23090588

Family Applications (1)

Country Status (8)

Cited By (2)

Families Citing this family (5)

Citations (2)

• 1989
  • 1989-11-23 ZA ZA898951A patent/ZA898951B/xx unknown
  • 1989-12-05 EP EP19890312655 patent/EP0376511A3/de not_active Ceased
  • 1989-12-06 GB GB898927571A patent/GB8927571D0/en active Pending
  • 1989-12-12 JP JP1322455A patent/JPH02212579A/ja active Pending
  • 1989-12-12 CA CA002005237A patent/CA2005237A1/en not_active Abandoned
  • 1989-12-14 AU AU46731/89A patent/AU616825B2/en not_active Ceased
  • 1989-12-14 FI FI895986A patent/FI895986A0/fi not_active Application Discontinuation
  • 1989-12-15 BR BR898906516A patent/BR8906516A/pt unknown

Patent Citations (2)

Also Published As

Similar Documents

Legal Events